


What, What?

by were_lemur



Category: Supernatural
Genre: F/M, Merry Month of Masturbation Challenge 2016
Language: English
Status: Completed
Published: 2016-05-18
Updated: 2016-05-18
Packaged: 2018-06-09 04:56:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 472
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6891094
Author URL: https://archiveofourown.org/users/were_lemur/pseuds/were_lemur
Summary: <blockquote class="userstuff">
              <p>One of Dean's hook-ups convinces him to try something new.</p>
            </blockquote>





	What, What?

Her name had been Jenny, or maybe it had been Janie, and she'd taken Dean back to her art studio from the bar. She'd pulled him on top of her, and inside her, and then just when he'd been getting into it, she'd dragged her fingers down the cleft of his ass.

He'd been surprised, to say the least. But he'd been fucking her slow and easy and she'd been sucking his tongue into her mouth and so it had seemed like too much trouble to say _hey, maybe we should reconsider this_ when Judy or whatever her name was brushed her finger against his asshole.

When she'd pressed a slicked fingertip into the opening, though, he did hesitate. But June had clenched her inner muscles on him and he'd stopped thinking with his upstairs brain, the part of him that was telling him, _you know, guys don't like anything in the butt_ because once he'd got past the initial shock of it, it actually did feel pretty nice.

Once she'd gotten her finger all the way inside him, she'd started rubbing in little circles, and damn, that had felt good. It was like whiskey, the good stuff, and when he'd come he'd been left twitching and making disconnected half-words until his world finally sorted itself out.

He'd left Joan and headed back to the motel room, and he'd thought that would be the end of it.

Until a few days later when he was jerking off in the shower, and he thought, _you know, I should try that again._

He used a good dollop of Sam's detangling conditioner on his finger, and then started to grope himself. The angle was awkward, but he finally managed, hunching awkwardly over and pressing his finger back between his legs.

Once he got his fingertip past the ring of muscle, though, the rest of his finger just sank in. He made a little sound in the back of his throat at the feel of it. He curled his finger and moved it experimentally. Then started stroking his cock again. Doing both at the same time was awkward; the masturbatory equivalent of patting his hand and rubbing his stomach, but after an awkward couple of minutes, he got into the rhythm of it.

His orgasm took him by surprise; he nearly overbalanced into the wall.

By the time he caught his breath, the shower was barely lukewarm. He washed his hands -- twice -- then dried off and pulled on his clothes.

Sam looked up at him for a long moment, and he felt like retreating back into the bathroom to hide. But then he decided; what the hell. It was the twenty-first century. A man could like the occasional finger up the butt if he wanted to.

As long as his little brother never, ever found out.


End file.
